56272-57-2Relevant academic research and scientific papers
Synthesis and Evaluation of Antiviral Activity of 2'-Deoxyuridines with 5-Methylene-2-thiohydantoin Substituents in the 5-Position
El-Barbary, A. A.,Khodair, A. I.,Pedersen, E. B.,Nielsen, C.
, p. 593 - 598 (2007/10/02)
1-(2-Deoxy-3,5-bis-O-(4-methylbenzoyl)-D-erythro-pentofuranosyl)-5-formyluracil (4) was synthesized from 5-formyluracil and an appropriate methyl glycoside and condensed with 2-thiohydantoin (5a) and its corresponding 3-phenyl derivative 5b to give 5--2-thiohydantoins 7a and 7b, respectively, in 65-70percent yield.They were deprotected with sodium methoxide in methanol to give both anomers of the free nucleosides.In a different route 5-formyluracil (1) was condensed with 5b and subsequently with an appropriate methyl glycoside to give 7b. - Keywords: 2'-Deoxyuridines; 2-Thiohydantoins; Nucleoside synthesis; Antiviral activity.
Synthesis of Uridine with Methylene-2-thiohydantoin as 5-Substituent
El-Barbary, Ahmed A.,Khodair, Ahmed I.,Pedersen, Erik B.,Nielsen, Claus
, p. 619 - 622 (2007/10/02)
5-Formyl-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)uracil (4) was synthesized from 5-formyluracil (2) and 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose (3) and condensed with 2-thiohydantoin derivatives 5 by using piperidine as the catalyst to give 5-(uridin-5-yl
Synthesis of 2',3'-dideoxy-3'-fluorouridines with potential anti-HIV activity according to neural network calculations
Sofan,Abdel-Megied,Pedersen,Pedersen,Nielsen
, p. 516 - 520 (2007/10/02)
Methyl 2, 3-dideoxy-3-fluoro-5-O-(4-phenylbenzoyl)-β-D-erythropentofuranoside was condensed with trimethylsilylated 5-substituted uracils to give nucleosides using trimethylsilyl trifluoromethanesulfonate as catalyst. In the case of 5-nitrouracil an acyclic nucleoside believed to be an intermediate for the corresponding nucleoside was isolated. The 5-substituents were selected from neural network calculations on compounds with potential activity against HIV-1. All compounds from the condensation reactions were deacylated by treatment with sodium methoxide in methanol.
